


180 Degrees, Caught In Between

by Minxchester (ComeAlongPond14)



Series: A Criminally Hot Love Story [12]
Category: Supernatural
Genre: Anal Fingering, Anal Gaping, Anal Sex, Come Eating, Come Marking, Come Sharing, Come Swallowing, Dirty Talk, Double Penetration, Foursome - M/M/M/M, M/M, Multi, Oral Sex, Past Relationship(s), Slut Gabriel, Spitroasting, Wincest - Freeform
Language: English
Status: Completed
Published: 2017-05-13
Updated: 2017-05-13
Packaged: 2018-10-31 04:45:26
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,522
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/10891971
Author URL: https://archiveofourown.org/users/ComeAlongPond14/pseuds/Minxchester
Summary: "...if he takes two dicks he needs ‘em to be nice and real--don’t you, sweetheart?”





	180 Degrees, Caught In Between

**Author's Note:**

> I had writer's block, but I beat it with a stick!
> 
> Title, once more, from "3" by Britney. <3

Sitting up against the headboard of their hotel room bed, Sam had Gabriel on all fours above him, facing away from his Dom. Four of Sam’s fingers were working slowly, lazily in and out of his hole. “Goddamn, you gape so much when you’re nice and worked open,” Sam purred, taunting him softly. “I bet even my cock is gonna end up not being enough for such a cockslut hole, one day.”

Gabe stuttered on a choked laugh, but he didn’t even try for any kind of legitimate protest to the other man’s words, arching his back to continue taking Sammy’s fingers in and out, deeper and deeper on every thrust.

Dean sat in one of the dinette chairs, pulled over to the foot of the bed, watching his brother and absently stroking Cas’ hair while the submissive himself sat naked on the floor between his Master’s feet. His cock was hard, and Dean had him stroking it intermittently with a murmured order to continue--but it was done with more of a goal of sustained, sleepy pleasure than with any real focus on letting him come any time soon.

The older Winchester laughed when Gabe failed to argue, meeting his little brother’s eyes above the smaller brunette’s head. “Hard to imagine that monster dick of yours ever not bein’ enough for him--but maybe you could work some fingers in alongside it sometime, just to test out the theory, huh, Sammy?”

Sam licked his lips at the suggestion, tilting his head and examining his fingers as they worked in and out of Gabe’s ass. “You know what, De...I’m not even sure _that_ would be enough. You should see his ass right now...hungry hole, practically swallowing my fingers and still leaving some room for more...”

He paused there, but his big brother knew; he always knew what Sammy was really thinking. And when it was a fucking hot idea, Dean never left it alone. “You think he could take two cocks at once, don’t you, Sammy,” he purred, his grin widening slowly and wickedly.

Gabriel instantly let out a low, keening whine at the words, and at Dean’s feet, Cas shifted, his blue eyes opening to glance first up at his Master, then over at Sam and Gabriel, expression remaining curious and neutral.

Sam nodded, smirking over at Dean, and he slowly dragged his fingers back out of Gabriel all the way. “I do,” he admitted, wiping the lube still on his fingers off against Gabe’s ass. “Thought about--using one of the dildos while fucking him, but I think...I think we can make it a little more authentic for him, don’t you?”

Dean chuckled at that, sitting forward and guiding Cas’ head to one side, so that his cheek rested against the older Dom’s thigh. Cas relaxed at once, letting Dean direct his movements as he pleased, like he always did. “Oh, we definitely can,” Dean replied. “Needy thing like Gabriel, if he takes two dicks he needs ‘em to be nice and real--don’t you, sweetheart?”

Gabe whimpered and nodded, lifting his head heavily to stare back at Dean as he wriggled his hips, trying to get Sam’s attention back on his hole. “If--if that’s what you boys wanna do to me next, then yeah--it’s gotta be the real deal.”

Dean smirked knowingly, then looked down at Cas thoughtfully; his lover simply blinked back at him languidly, waiting for Dean’s instruction. Dean could read the submissive man’s face like a book; it was clear that Cas was wondering which of them Dean planned on having double up with Sam in fucking Gabriel.

“Last time that we made him wait for a while,” Dean said thoughtfully, nodding down toward Cas to indicate which submissive he meant. “Didn’t we say he’d get rewarded by having your boy’s mouth on his cock?”

Sam’s smile widened slightly at the direction that this was heading, and he stroked one hand gently over Gabriel’s flank as he answered. “Yes, I do believe we did. Is that how we’re doing it, De?”

The older Winchester nodded leisurely, licking his lips. “I think it’s a good possibility. Bettin’ the boys would enjoy it.”

Gabriel managed to interject at that point, his voice more than slightly strained. “If you’re saying what I think you are, then I for one will really fucking enjoy it. Had a feeling about you two.”

Dean snorted dismissively, giving him a bemused look. “Whatever you’re imagining, it’s probably not nearly that exciting, sweetheart.” He curled his fingers into Cas’ hair, tugging lightly, and smiled warmly when the kneeling man looked back up at him with contented eyes. “You’re down with that, angel?”

Cas’ lips curled up smugly at the corners. “Have been since you brought me back to Sam the very first time, sir.”

Sam’s voice was soft. “ Right now, De?”

Dean nods, waving him on. “Work Gabe open some more. See just how needy you can get that pretty, smart-mouthed bitch of yours,” he ordered his brother, ignoring Gabriel’s whine as Sammy chuckled and nodded, getting right to it.

Nudging Cas to turn around within the space between his knees, Dean cupped the other man’s face, and held his gaze intently. “You knew all along, huh?”

Cas shrugged delicately, tipping harder into his master’s touch and smiling softly. “It’s just--always been that way, since the first time. When you two shared me. I took it as a given.”

“And that is a story that I still need to hear in detail,” Gabe called out from the bed, and Dean laughed, glancing up at him through his lashes.

“Eventually,” he agreed. “You and Cas can chat about that.”

Gabe huffed at the brush-off of his question--then he gasped, distracted, when Sam twisted his fingers punishingly inside of him, rubbing right over his prostate. “Fuck,” the smaller brunette whimpered. “Yeah--well--that--and also how you two--got started.”

“An even longer story, depending on what _start_ you’re referring to,” Dean replied, laughing again. “We’ve had plenty of adventures of all different kinds, after all. But for now, let’s just focus on getting that ass of yours ready for both us big bad boys, huh?”

Gabriel scoffed at Dean’s words, but he didn’t try to keep arguing. He clenched his hands into the bed sheets, losing himself in Sam’s touches as the younger Dom continued skillfully opening his hole as wide as he could manage to.

Dean stood, moving a few feet forward to wait beside Cas and then stopping to watch Sam and Gabriel from there; Cas slid one hand up the inside of his master’s thigh, fingers curling over the denim in a delicate grip while Dean gently petted through his dark hair in tender affection.

Sam looked up at his brother, his wrist flexing as he fucked his fingers into Gabriel’s ass, then gradually slowed to a stop. “I think he’s ready for us both, De.”

Dean patted Cas’ head, a wordless command, and the kneeling man obeyed by remaining where he was as the older Winchester prowled forward, reaching the side of the bed and surveying Gabriel’s entrance as his brother’s fingertips played around the gaping rim.

“If he ain’t yet, he’ll get there quick enough,” Dean murmured in reply, grabbing the lube from the bedside table--they’d taken to just buying the largest bottle in the nearest convenience store, at this point--and pouring some more onto Sammy’s fingers. “Get underneath him, Sammy. Facing the other direction.”

His brother nodded at once, shifting back until he could pull his legs out from between Gabe’s widespread thighs and hands. He twisted around, sliding his head and upper body beneath Gabe’s until he could stretch out beneath him, aligning their bodies. Sammy closed his lube-slick fingers around his own cock, starting to stroke lazily as Gabe grinned down at him smugly, clearly excited over what was coming.

Dean turned back toward Cas, jerking his chin in invitation at his lover. “Come here, angel.”

Cas rose gracefully to his feet and padded forward immediately, accepting his master’s hand and letting Dean assist the smaller man up onto his knees on the bed, inches from both Sam and Gabriel’s heads. Without being told to, Cas went still, waiting for his Dean’s continued guidance.

Kissing him once more in approval, the press of his lips hard and brief against Cas’, Dean turned away and crawled over to kneel between Sam and Gabriel’s overlapping legs, tilting his head enjoy the view in full. “God, I’ll never get tired of this.”

Gabriel hummed, glancing over his shoulder to smirk at the older man. “Take a picture, it’ll last longer.”

“Well, one: I think it lasts the same amount of time--don’t pretend that you’re not more than happy to strip down and bend your ass over the minute me or Sammy wants a piece of you. And two: I also think that I will do exactly that.” Dean grinned wickedly, reaching to the bedside table and grabbing his phone. He opened the camera app, aiming it at Gabe’s ass, and the shutter clicked loudly as he snapped the photo.

From underneath Gabriel, Sam huffed out a laugh, still stroking his cock.  “Quit playing photographer and get a move on.”

“Patience,” Dean chided teasingly, reaching down to give his brother’s inner thigh a fond smack through the vee in Gabriel’s legs. “I’m gonna make this worth the while for all of us, and you know it.” Sam sighed dramatically, but Dean just smirked. “Always the impatient one. I’m amazed you ever developed the stamina you have.”

“Well, I did learn from the best,” Sam shot back fondly, and Dean barked out a laugh.

“That you did, bitch.”   

”Jerk.” It was said so affectionately, as if he had said _I love you_ rather than a would-be insult, and Dean’s eyes were soft as he traded a smile with his brother over Gabriel’s shoulder.

Grabbing the lube, Dean poured some into his palm and reached down between Gabriel’s legs to slick it over Sam’s cock, making his brother grunt quietly at the added stimulation of a second hand on himself. “Go on and take ‘im, Sammy.”

His brother obeyed at once, gripping his cock and guiding it into Gabe’s hole, and the smaller brunette whined, deep and low, as his ass was slowly penetrated. “Fuck, _finally_...”

Dean smirked, leaning to one side to reach up and grip Gabriel’s jaw, pressing at the joint with his thumb in order to make him whine quietly again at the almost-pain. “You are _such_ a mouthy bitch,” Dean told him, but he was grinning, affection rippling through the words. “Gonna need to put that waggin’ tongue to better use. Angel, come over here.”

Cas shifted forward obligingly, and Dean moved his hand to slide it into Gabriel’s hair, encouraging him to meet the other submissive halfway. Gabe heeded the unspoken order at once, bending forward and lapping at Cas’ cock until he could sink his mouth down around it, taking inch by inch until he was at the base--and then he drew back, continuing sliding up and down in long, teasing movements.

Cas groaned softly, head falling back and eyes hooding, watching Dean over Gabriel’s head and back as the other submissive sucked hungrily at his cock.

“That feel good, sweetheart?” Dean purred, and Cas nodded, reaching out with one shaky hand to squeeze his master’s fingers.

“Yes, sir...”

“Good,” Dean said contentedly, releasing his lover’s hand and moving back to return his attention to Gabriel’s hole, where Sammy’s dick was still sliding leisurely in and out of the well-stretched muscle.

Dean reached out, sliding his index and middle fingers around the flexing rim, feeling how Gabriel was tightening and squeezing around Sammy’s cock. Sam’s shaft grazed his fingertips as he kept fucking slowly in and out, and Dean licked his lips at the sight, then bent forward and began running his tongue wetly around where Sam was thrusting into the smaller man.

“Shit,” Gabe panted out in shock, his back flexing as his nerves reacted to the added touch and wetness. “Oh, shit, yes, that, that is filthy, feels so good...” He started rolling his hips harder, fucking himself up and down on Sam’s cock just to feel Dean’s tongue against his rim; Dean allowed it for a moment, simply running his tongue lazily over all the flesh he can reach.

Eventually, though, he lifted his face, ignoring Gabriel’s low whine and sliding his hand over where his mouth had been, fingertips testing the give of the smaller brunette’s entrance as Sam kept on fucking him. “Think I’ll fit in there alongside you, Sammy?”

“Don’t see why not, De,” his brother panted conversationally, grinning. “He’s a loose little slut, after all.” Gabriel merely hummed his agreement at that assessment, utterly unashamed, making both brothers laugh.

Kneeling upright, Dean grabbed the lube again and applies some to his own cock. Shifting in closer to their twitching bodies, he gripped the shaft and teased the head against the edge of Gabriel’s rim, watching the muscle flutter and clench at the hint of additional penetration.

“If it feels like too much, you call it,” Dean said quietly, his voice laden with command. Gabriel shuddered and nodded, dropping forward until his chest is nearly pressed flat against Sam’s, which effectively forced his mouth all the way down around Cas’ dick. He let out a throaty moan around the hard length, and Dean grinned, spanking his ass for trying to distract himself from what was coming his way.

Cas cried out at feeling Gabe’s throat flexing around him, his head falling back in sheer bliss, and Dean grinned wider as he watched his boy. His eyes remained on Cas, and Dean pushed forward, rolling his hips in short, punctuating thrusts--until with a soft groan from Gabriel, the head of Dean’s cock breached him, and both Gabriel and Sam moaned simultaneously as Dean slipped inside of Gabe alongside his brother’s dick.

They found their pace in minutes, thrusting at alternate rates to make sure that they were both fitting comfortably in the snug channel of Gabriel’s ass. “Shit,” Sam grunted, his hazel eyes fluttering. “ _Shit_ , that is so fucking tight, De...’s amazing...”

“It really is,” Dean agreed, breathlessly. “Jesus, why haven’t we done this lately, Sammy?”

His brother snorted a laugh. “We’ve only done this with pussies before now. God, this is good, might even be better...”

Gabriel growled around Cas’ cock as he listened to their exchange, his toes curling as he pushed his hips up higher, as if begging for the brothers to go harder inside of him. Dean laughed again at his reaction, slapping Gabe’s ass harder and then fucking balls-deep into him, cursing under his breath as he felt his cock grinding up against Sammy’s inside of Gabriel. “Think that might have more to do with sentiment than sensation, little brother.”

Sam merely shrugged in allowance of that possibility, bracing his feet flat on the bed and then thrusting all the way inside of Gabriel before he stilled, leaving it to Dean to continue the real fucking. His brother nodded wordlessly, finding one of Sammy’s hands on Gabriel’s thigh and giving it a tender squeeze of affirmation before he got right to work, fucking into Gabriel as hard and as fast as he could manage with the added tightness of his shared ass.

In front of him, Cas let out a strangled whine as Gabriel’s throat contracted in response to what was happening to his body. “Sir--I--I think I might--”

Dean looked up at him, taking in his trembling state, and he nodded, grinning at Cas. “Come with me, angel,” he breathed out, and Cas met his eyes, hunger bright in his face. “Let’s come together, let’s cream this pretty bitch at both ends, huh?”

With a cry, Cas nodded, throwing one hand out above Gabriel’s head as it continues bobbing up and down his shaft. Dean caught his fingers with the hand that wasn’t still pressed over Sammy’s on Gabriel’s hip, and he held on deathly-tight as his boy came for him, Cas’ release spilling over Gabriel’s lips and down the column of his throat, a little splashing onto Sammy’s chest as Gabe choked, and tried to swallow whatever he could.

Watching Cas writhe through his orgasm pushed Dean over in seconds, and he came as well, shuddering as he buried himself inside of Gabriel to ride it out.

“Fuck,” Sam moaned from underneath them all. “Oh, _fuck_ , De, I can feel your come against my dick--it’s like--extra lube--it’s so fucking _hot_ , though--”

Dean grinned weakly, slumping over Gabriel’s back and rutting forward just to feel the soppy heat that Sammy was describing. “Hell yeah, it is. Come on, Sammy, you gonna come inside there, too? Gonna make that bitch of yours take two loads at once?”

“Shit, _yes_ , I am,” Sammy whimpered, planting his feet more securely and thrusting up, hard. He came with a shout, and Gabriel cried out as well, Cas’ come still sliding messily over his cheeks and down the front of his throat.

From where he was kneeling, Dean cursed as he witnessed the display. “It is literally fucking gushing out of him, Sammy, you’re--oh, fuck,” he panted, jolting slightly as his cock slipped loose, and Dean moved away from them with a shaky laugh. “Your come just literally fucking pushed me out of him, Sammy, that’s how stuffed full we got him. _Holy_ _shit_ is right.”

Sam merely laughed in acquiescence, sounding utterly exhausted; with a low whine, Gabriel pitched off of him and landed on his side.

Dean pounced on him immediately, grabbing his higher leg and tugging it up, exposing Gabriel’s well-creamed hole. Cas scooted down the bed to kneel beside Dean between Sam’s still-sprawled legs, and he looked at the brothers’ handiwork with an admiring chuckle.

“‘M I a fuckin’ mess?” Gabriel asked them smugly, and both Dean and Cas laughed at his obvious pride in his current state.

“It won’t even all fit inside you,” Cas murmured, his tone reverent. “God, you’re dripping at both ends.”

Gabriel merely preened, and Sam reached down, gathering some of Cas’ come off of his own chest and reaching out to smear it sloppily over Gabriel’s mouth, adding to the mess lingering there.

“You’ve been fucked full and pumped to bursting with all three of us,” he said happily. “Shit. De, get a photo of him like that, he’s perfect.”

Dean nodded and complied, grinning when Gabriel eagerly spread his own legs with his hands behind each knee, and opened his mouth wide, tongue thrusting out to show off the slick white that was still filling his mouth. “Proud of being a double penetration, spit-roasted whore?” Dean teased, clicking over to the video option to preserve this moment.

Gabriel nodded at once, winking at the lens as he was recorded. “‘M _always_ happy to be a whore for you boys."

* * *

It was only after they were all cleaned off, dried, and sprawled naked back in bed together that Gabriel lifted his head, arching his eyebrows slightly. “You thought I’d forget again that I still want to hear your backstory,” he accused, and Dean snorted in response.

“No, I know you’ll keep on asking,” he laughed. “We will tell you. You just gotta _earn_ it.”

“Pretty sure he earned something tantalizing today,” Sammy rasped drowsily, and Cas hummed an affirmation, making Dean bark a laugh at having them gang up on him.

“Alright, alright, seems I’m outnumbered,” he joked. “Gabe, you can ask Cas about how he landed his ass in our bed--that’s a long story with lots of varied details, and I’m sure he has his own commentary for it. But you also wanted to know more about just me and Sammy, didn’t you?”

Gabriel turned to grin at Dean from where his head was resting on the small of Cas’ back, while the other submissive was on his belly, pillowing his arms and head on Sam’s chest at the foot of the bed. “Hell yes. Have you two always been a little bit...more?”  
Dean shook his head, while Sammy let out a quiet laugh and murmured, “Nope.” Glancing over at Cas’ face, Dean could tell that he, too, was curious about this part of their story; Dean caved with a smile, folding his hands beneath his head.

“Did it start at the same time that your epic crime career did?” Gabriel persisted, and Cas reached out, placing one finger lightly over his lips, hushing him. Gabe quieted with a playful growl of impatience, and Dean grinned at them both, sitting up and reaching out to pet a hand fondly through Cas’ hair as he answered Gabriel.

“Well, the first time we pulled a _job_ wasn’t till Sammy dropped outta college--we were already in our 20s. But the first time we shared a lover was as teens--and this may be a shock, but it was actually a girl...”

**Author's Note:**

> Next up: We shall visit the very first person to be shared by the brothers. She'll make you realize why he prefers "Cas" to "Cassie" as his current lover's nickname. XD


End file.
